Record Information
Version1.0
StatusDetected and Quantified
Creation Date2021-11-19 04:36:05 UTC
Update Date2024-04-20 06:15:50 UTC
Metabolite IDMMDBc0033133
Metabolite Identification
Common Nameudp-galactose
DescriptionUridine diphosphategalactose (UDPgal) is a nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. UDPgal is a pivotal compound in the metabolism of galactose. UDPgal is a product of the galactose-l-phosphate uridyl transferase (EC 2.7.7.10) reaction but may also be made from Glucose-l-P, involving uridine diphosphate galactose-4-epimerase (EC 5.1.3.2). UDPgal is the necessary galactosyl donor of galactose in the metabolism to incorporate it into complex oligosaccharides, glycoproteins and glycolipids (galactosides). Defective galactosylation of complex glycoconjugates exists in tissues from galactosemic patients. There is a tendency for galactosemic red cell UDPgal to be in the low normal range with a high uridine diphosphate glucose to UDP-gal ratio. This may reflect an inability of red cell UDPgal-4'-epimerase to maintain a normal ratio and consequently higher levels of UDPgal. In the more complex white blood cells and cultured fibroblasts, the UDPgal content and the uridine diphosphate glucose to UDPgal ratio of galactosemics are normal. Therefore, defective galactosylation observed in galactosemic fibroblasts must result from a defect in the transfer of galactose from UDPgal to these moieties. (PMID: 2122114 , 7671968 ).
Structure
SynonymsNot Available
Molecular FormulaC15H24N2O17P2
Average Mass566.3018
Monoisotopic Mass566.055020376
IUPAC Name[({[(2R,3S,4R,5S)-5-(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid
Traditional Name{[(2R,3S,4R,5S)-5-(2,6-dioxo-1,3-dihydropyrimidin-4-yl)-3,4-dihydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid
CAS Registry Number2956-16-3
SMILES
OC[C@H]1O[C@@H](OP(O)(=O)OP(O)(=O)OC[C@H]2O[C@H]([C@H](O)[C@@H]2O)C2=CC(=O)NC(=O)N2)[C@H](O)[C@@H](O)[C@H]1O
InChI Identifier
InChI=1S/C15H24N2O17P2/c18-2-5-8(20)10(22)12(24)14(32-5)33-36(28,29)34-35(26,27)30-3-6-9(21)11(23)13(31-6)4-1-7(19)17-15(25)16-4/h1,5-6,8-14,18,20-24H,2-3H2,(H,26,27)(H,28,29)(H2,16,17,19,25)/t5-,6-,8+,9-,10+,11-,12-,13+,14+/m1/s1
InChI KeyUSAZACJQJDHAJH-QFIAFIRLSA-N